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Tomé, A. C., Science of Synthesis, (2004) 13, 561.
Benzotriazole is rapidly converted into crystalline 1-chloro-1H-1,2,3-benzotriazole (682, X = Cl) by treatment with sodium hypochlorite in aqueous acetic acid (Scheme 248).[692] Similar reaction with sodium hypoiodite in aqueous sodium hydroxide gives 1-iodo-1H-benzotriazole in 43% yield.[687] Alternatively 1-iodo-1H-benzotriazole is obtained in 94% yield by treatment of 1-chloro-1H-benzotriazole in dichloromethane with 1 equivalent of iodine.[687] Similarly, 1-bromo-1H-benzotriazole is prepared in 80% yield by the addition of 1-chloro-1H-benzotriazole to a solution of bromine in dichloromethane.[687] Addition of sodium hypochlorite to a solution of 4,5,6,7-tetrachloro-1H-benzotriazole in glacial acetic acid, at room temperature, rapidly affords N,4,5,6,7-pentachloro-1H-benzotriazole (because of the extreme insolubility of this compound, the position of the fifth chlorine at N1 or N2 was not assigned unambiguously).[687]
Meeeee 888 Meeeeeeee ee 8-Meeeee- eee 8-Meee-8M-eeeeeeeeeeeee[888,888]
8M-Meeeeeeeeeeee ee eeeeeeeeeee ee 8,8,8,8-eeeeeeeeeee-8M-eeeeeeeeeeeee (888, M = Me) ee 88% eeeee ee eeeeeeeee eeee eeee eeeee (e eeeeeee ee eeeeeeeeeeee eeeeeeeeeeee eeee eee eeeeeeeeeeee eeeeee eeee) eee eeeee eeeee (Meeeee 888).[88] Meeee eeeeeee eeeeeeeeee, 8-eeeeee-8M-eeeeeeeeeeeee eeeee 8,8,8,8-eeeeeeeeeee-8-eeeeee-8M-eeeeeeeeeeeee ee 88% eeeee[88] eee eeeeeeeeeeee ee 8-eeeeee-8M-eeeeeeeeeeeee eeee eeee eeeee eeeeeeee eeeee eeee ee eeee 8,8,8,8-eeeeeeeeeee-8-eeeeee-8M-eeeeeeeeeeeee ee 88% eeeee.[888] Meeeeeeee 8-eeeee-8M-eeeeeeeeeeeee eeee eeee eeeee eee eeeee eeee eeeeeee 8,8,8,8-eeeeeeeeeee-8M-eeeeeeeeeeeee (88%), eee 8,8-eeeeeeee-8M-eeeeeeeeeeeee eeeee 8,8,8,8-eeeeeeeeeee-8-eeeeee-8M-eeeeeeeeeeeee (eeeee eee eeeeeeee); ee eeeee eeeeeee eee eeeeeeeeeeee ee eee eeeeeeee eeee eee eeeeeeee ee eeeeeeee.[888]
Meeeee 888 Meeeeeeee ee 8,8,8,8-Meeeeeeeeee- eee 8,8,8,8-Meeeeeeeee-8M-eeeeeeeeeeeee[88,888]
Meeeeeee ee 8M-eeeeeeeeeeeee eeee eeeeeee ee eeeeeeeeeeee eeeeee eeee eeeee eeeeee eeeeeee 8,8,8,8-eeeeeeeeee-8M-eeeeeeeeeeeee ee 88% eeeee (Meeeee 888).[888] 8-Meeeee- eee 8-eeeeee-8M-eeeeeeeeeeeeee eee eeeeeeeeee ee eee eeee eee eeeeeeeee, eeeeeeeeeeee, 8,8,8,8-eeeeeeeeee-8-eeeeee-8M-eeeeeeeeeeeee (88% eeeee) eee 8,8,8,8-eeeeeeeeee-8-eeeeee-8M-eeeeeeeeeeeee (88% eeeee).[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8M-eeeeeeeeeeeee (888, M = Me); Meeeeee Meeeeeeee:[888]
MMMMMMM: 8-Meeeee-8M-eeeeeeeeeeeee eeeeee eeeeeeeee eeee MMMM.
8 M MeMMe (88 eM, 8.8 eee) eee eeeee eeeeeeee ee ee ee e eeeeeee eeee ee 8M-eeeeeeeeeeeee (88 e, 8.88 eee) ee ee MeMM (8:8). Meeee eeeeeeee eeee M8M eee eeeeeeeee eeeee eee eeeeeeeee eee eeeeeeeeeeeeee eeee (MM8Me8/eeeeeeeee eeeee) ee eeee eeee (888, M = Me) ee eeeeeeeee eeeeeee; eeeee: 88 e (∼888%); ee 888–888°M.
8,8,8,8-Meeeeeeeeee-8M-eeeeeeeeeeeee (888, M = Me); Meeeeee Meeeeeeee:[88]
M eeee ee 8M-eeeeeeeeeeeee (8.88 e, 8.888 eee) ee e eeeeeee ee eeeee MMe (888 eM) eee eeeee MMM8 (888 eM) eee eeeeeeee eee 8 e, eeeeee, eee eeeeeee ee eeeeeeeeeee eee eeeeeee; eeeee: 8.8 e, (88%). Meeeeeeeeeeeeeeee (MeMM8) eeee e eeeee eeeeeeeeeee eeeee; ee 888–888°M.
References
| [16] | Meeee, M. M.; Meeeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [585] | Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [687] | Meeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
| [692] | Meee, M. M.; Meeee, M. M., M. Meee. Mee. M, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 888.
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